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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 23
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Original Articles

Atypical Oxidation Reaction by Thionyl Chloride: Easy Two‐Step Synthesis of N‐Alkyl‐1,4‐dithiines

, , &
Pages 3591-3597 | Received 17 Jan 2006, Published online: 24 Nov 2006
 

Abstract

Easy two‐step synthesis of a series of dithiines was performed from succinic anhydride via cyclization of the corresponding 4‐(alkylamino)‐4‐oxobutanoic acids (succinamic acids). The reaction, carried out in polar aprotic solvents, gave 4,8‐dithiine‐indacene‐1,3,5,7‐tetraones (diimides 3) via 3,7‐bis‐4,8‐dithia‐indacene‐1,5‐diones (diisoimides 2), which could be isolated. Surprisingly, in this reaction, thionyl chloride appeared as an oxidant, and this process seemed to be useful for the syntheses of S‐containing heterocyclic compounds such as 1,4‐dithiins. A mechanistic pathway was considered.

Acknowledgments

We gratefully acknowledge Dr. Masson and Dr. Gulea (Laboratoire de Chimie Moléculaire et Thio‐organique, Caen, France) for helpful discussions about the mechanistic pathway.

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